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Rachel Sklar

Bachelor of Laws (LLB) 1998

“Life is a cabaret, old chum,” the lyrics to the 1966 musical suggest, and Rachel Sklar has enjoyed a number of interesting roles.

Sklar, who developed a passion for musicals during a childhood of summer camp performances, was tempted by thoughts of a career in theatre, but opted for the U of T Faculty of Law instead.

“I loved law school,” Sklar said. “I was very well suited to the thinking, conversations and grappling with ideas that was required, and I wrote well and fast, which was a positive.”

She also enjoyed performing with fellow students in the Law School Follies, an opportunity to indulge her love of theatre. For the 50th anniversary of the Follies, Sklar penned song lyrics and flew home from a posting in Sweden to perform it with her classmates.

Sklar’s first job as a lawyer required her to move to New York City and she has settled there. After a few years in law, she made a move to the media, joining the fledgling Huffington Post at a time when social media was not yet ubiquitous. Sklar did live blogging of the 2008 presidential debates and often substituted for Arianna Huffington in media interviews, making a name for herself as a commentator with a feminist perspective.

“I’ve always been righteously indignant about things that don’t seem fair, and my feminism was activated by the double standard in media coverage during Hillary Clinton’s first run for the presidential candidacy,” Sklar said. “I felt indignant on her behalf and on behalf of myself and other women.”

Today, Sklar is the co-owner of a social media-based women’s networking firm, TheLi.st, which allows for a flexible schedule while she takes on her newest role: a proud New York City single mother raising a young daughter.

“New York is really a city of opportunity and I am living proof that whatever your interests, you can form a network, create and participate,” Sklar said.